Acetic Acid → HCID 178478216, compound

HRID 397838Notes

Reaction equation

HRID 397838 reaction equation
[Cl:1][C:2]1[CH:45]=[C:44]([Cl:46])[CH:43]=[CH:42][C:3]=1[O:4][C:5]1[CH:41]=[CH:40][CH:39]=[CH:38][C:6]=1[CH2:7][O:8][CH2:9][CH:10]1[CH2:37][CH2:36][C:13]2[N:14](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[CH:15]=[N:16][C:12]=2[CH2:11]1.ClC1C=C(Cl)C=CC=1OC1C=CC=CC=1COCC1CCC2N=CN(C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)C=2C1.C(O)(=O)C>O>[Cl:1][C:2]1[CH:45]=[C:44]([Cl:46])[CH:43]=[CH:42][C:3]=1[O:4][C:5]1[CH:41]=[CH:40][CH:39]=[CH:38][C:6]=1[CH2:7][O:8][CH2:9][CH:10]1[CH2:37][CH2:36][C:13]2[NH:14][CH:15]=[N:16][C:12]=2[CH2:11]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 23001233HCID 23001233, compoundHCID 23001270HCID 23001270, compound

Product 1

HCID 178478216HCID 178478216, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

A soution of a mixture of 5-[2-(2,4-dichlorophenoxy)benzyloxymethyl]-1-triphenylmethyl-4,5,6,7-tetrahydro-1H-benzimidazole and 5-[2-(2,4-dichlorophenoxy)benzyloxymethyl]-3-triphenylmethyl-4,5,6,7-tetrahydro-3H-benzimidazole (356 mg, 0.55 mmol) in a mixture of glacial acetic acid (9 ml) and water (1 ml) was heated to 70° C. for 2 hours. The reaction mixture was cooled to room temperature. The solvent was removed in vacuo. The crude product was purified by flash chromatography on silica (80 g), using DCM/methanol/−25% aqueous ammonia as eluent, to give 175 mg of the title compound. HPLC method C: elution at 11.42 min.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customThe solvent was removed in vacuo
  3. customThe crude product was purified by flash chromatography on silica (80 g)

Sources & evidence

ORD record
ord-7b6b6be8f7114166973bef0d56e7f2c6
Source dataset
uspto-grants-2003_08
Patent number
US06610721B2

Reaction notes

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